Trifluoroacetic acid → 3-Methoxy-pyrrolidine-3-carboxylic acid [3-(2-methoxy-pyridin-4-yl)-1H-indazol-5-yl]-amide

HRID 1020949노트

반응식

HRID 1020949 반응식
C(OC([N:8]1[CH2:12][CH2:11][C:10]([O:52][CH3:53])([C:13](=[O:51])[NH:14][C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[N:20](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[N:19]=[C:18]3[C:43]2[CH:48]=[CH:47][N:46]=[C:45]([O:49][CH3:50])[CH:44]=2)[CH2:9]1)=O)(C)(C)C.C([SiH](CC)CC)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:50][O:49][C:45]1[CH:44]=[C:43]([C:18]2[C:17]3[C:21](=[CH:22][CH:23]=[C:15]([NH:14][C:13]([C:10]4([O:52][CH3:53])[CH2:11][CH2:12][NH:8][CH2:9]4)=[O:51])[CH:16]=3)[NH:20][N:19]=2)[CH:48]=[CH:47][N:46]=1

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 673434733-Methoxy-3-[3-(2-methoxy-pyridin-4-yl)-1-trityl-1H-indazol-5-ylcarbamoyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

생성물 1

HCID 673452223-Methoxy-pyrrolidine-3-carboxylic acid [3-(2-methoxy-pyridin-4-yl)-1H-indazol-5-yl]-amide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To the stirred solution 3-Methoxy-3-[3-(2-methoxy-pyridin-4-yl)-1-trityl-1H-indazol-5-ylcarbamoyl]-pyrrolidine-1-carboxylic acid tert-butyl ester 7BV (2.95 g, 4.16 mmole) in DCM (50 mL) at r.t. was added triethylsilane (1.00 ml, 6.24 mmole) followed by TFA (10 mL). The mixture was stirred at r.t. under dry N2 gas for 4-5 hours. The mixture was evaporated to dryness and co-evaporated with dry toluene (2×75 mL). The resulting crude solid was purified on RediSep 120 g cartridge eluting with 2.5%-6% 2M NH3-MeOH/CH2Cl2 to yield an off-white solid 8BV (1.23 g, 80%).

후처리

  1. customThe mixture was evaporated to dryness and co-evaporated with dry toluene (2×75 mL)
  2. customThe resulting crude solid was purified on RediSep 120 g cartridge
  3. washeluting with 2.5%-6% 2M NH3-MeOH/CH2Cl2
  4. customto yield an off-white solid 8BV (1.23 g, 80%)

출처 및 근거

ORD 기록
ord-5325f27f4a95453fb81f546b2185e492
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08716483B2

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